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Outlook Popping Up and Asking For Password - (XP SP3 and Exchange 2007)

I'm using Outlook 2007 SP2 on XP SP3 and I'm connecting to an SBS 2008 Server that is running Exchange 2007.

I occasionally get popups in Outlook asking me to enter my domain credentials so that Outlook can connect to the server. I'm logged into a domain user account and I'm on the LAN where the server resides. I can access other network resources with no problem including all network drives (they don't show disconnected either).

Most of the time Outlook works fine without popping up and asking for credentials.

When I do type in my username and password it doesn't seem to satisfy Outlook. Outlook continues to ask for more passwords and also pops up windows asking about certain certificates.

What could be causing this problem? How do I troubleshoot it?

Wasim Shaikh

Did you check this link?

https://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_2300-Outlook-continually-prompting-for-username-and-password.html

HKComputer

ASKER

I hadn't seen that yet but I think that will probably solve my problem. It's going to be a little while until I can read through that and apply and test all of it. But thanks any way.

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Glen Knight

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HKComputer

ASKER

OK, I resolved this problem by installing SP3 for Exchange 2007. I had to use the Installation Tool for SBS 2008 to install it.

I also resolved the security warnings I was getting by creating A records in the local server for autodiscover.mydomain.local and remote.mydomain.local. I also created A records at my hosting company for autodiscover.mydomain.com and remote.mydomain.com that point to the static IP where our Exchange Server is hosted. This allows remote "Outlook Anywhere" clients to function without warnings and errors.

Thanks for the great article. Just a little feedback here on this section:

To accompany this you must have an SSL Certificate that contains the autodiscover.domainname.com URL (whilst you can configure ways around this, it really isn’t worth all the hastle). So purchasing an SAN/UCC Certificate with the following names in is a must for Exchange 2007 and Exchange 2010:

It wasn't clear to me if you were talking only to customers that are hosting their own DNS/Domain Name. If no, then I have to say that I think I resolved this problem quite simply without purchasing an SSL Certificate by creating DNS records (as noted above) and by putting https://servername.domainname.local and https://remote.domainname.com in my trusted sites. Is it likely that I will still have Certificate errors or warnings with this configuration? I'm not aware that I'm having any.

Glen Knight

In an SBS environment the SLP or Service Locator Point is used for autodiscover so the internal A records you have created won't get used by clients that are attached to the domain.

The SAN/UCC certificate is recommended but not required for SBS to work correctly in the default configuration.

HKComputer

ASKER

>In an SBS environment the SLP or Service Locator Point is used for autodiscover so the internal A records you have created won't get used by clients that are attached to the domain.

I trust your word on this more than mine since I don't know much about. I did think that my internal A records stopped those certificate warnings. I guess I'll have to do some more testing.

I plan to put all clients on Exchange soon and I want to be sure that I don't get complaints about popups, warnings, and errors.

Glen Knight

If you have followed my article then you should be fine :)

I specified the SLP just for SBS which wasn't strictly true it's also used in non-sbs environments.

Alan Hardisty

This question has been classified as abandoned and is being closed as part of the Cleanup Program. See my comment at the end of the question for more details.